My favorite Celebrity Jeopardy! (yes, the exclamation mark's part of the title) moment is when they had Wolf Blitzer, Arianna Huffington, and Oliver Stone. Wolf Blitzer looked really embarrassed by Oliver Stone, though Arianna Huffington held her own pretty well. Oliver Stone would have, under ordinary circumstances, have been kicked out after the first round--he was at negative dollars--but it's the celebrity version, so they're nicer. And then he was the only one to get one of the extra-special dumbed-down Celebrity Jeopardy! questions in the final round, and he won. I'm pretty sure Wolf Blitzer was resisting the urge to hit him.
"Now everyone was giving her that kind of look UFOlogists get when they suddenly say, 'Hey, if you shade your eyes you can see it is just a flock of geese after all.'"
"You can't erase icing."
"I can't believe it doesn't work! I found it on the internet, man!"